Trovafloxacin is child's play. How about a real man's antibiotic,
vancomycin
Three ether-linked phenyls, two with chlorines, and that's not all - also a biphenyl - all from phenylalanine type residues that comprise a cyclic peptide, sort of like
polymyxin B from the common OTC double/triple antibiotic ointment. And also two weird ass sugars for good measure.
And chirality, well...
The complex structure of vancomycin incorporates three different types of chirality, with eighteen stereogenic centres, a biaryl axis, and two chloroaromatic rings whose restricted rotations introduce an element of planar chirality [...]
[ref]
It has actually had a total synthesis before, several in fact.
It works as a "reverse penicillin" - they both stop cell wall production by interrupting D-alanine-D-alanine dipeptide linkages, but where penicillin mimics the D-alanine-D-alanine dipeptide and blocks the linkage enzymes, vancomycin
binds the D-alanine-D-alanine dipeptide and makes it unable to react any further.
Also it is an "antibiotic of last resort" and there are few things that it will not kill, given IV. And if your infection is vancomycin-resistant, you are, as they say, in big trouble now.
Now, if we are playing the optical phallus measurement optimization activity (colloquially known as "dick sizing"), let me show you this. EPO or
erythropoeitin is a peptide horomone that promotes red blood cell production. It has a molecular weight of 35,000 or so, is mostly protien (linked amino acids) bur has some modifications too. The structure is drawn below with every amino acid in a circle to save space.
And there was some group in 2013, who through painstaking linking of amino acid to amino acid, made enough EPO to test in mice, and proved it was identical to the natural material. Boom, paper in
Science (the "original gangster" of science literature from the US, alongside
Nature from the UK, not the easiest thing to do, and usually a career hilight).
[ref].
